Breaking Down Oak Street Bootmakers’ New Trench Boot with Design Director, George Vlagos

After nearly five years of design and numerous prototypes, designer George Vlagos of Oak Street Bootmakers has created what may just be his finest boot yet, the Trench Boot ($426).

First, a little background on the humble Trench Boot. With American wartime roots, the Trench Boot first came into service as a replacement for the Russet Marching Shoe during World War I in 1917. The construction was simple: tanned cowhide, two soles studded with hobnails. An iron plate heel. No waterproofing. Its popularity would lead to improvements, and enhancements proposed by General John “Black Jack” Pershing would bring about a new name: the Pershing Boot.

Though we doubt the Oak Street Trench Boot will find its way into any of today’s Army Quartermaster shortlists, we can say with confidence that it has made it into ours. The Trench Boot features much of what you’ve come to expect in top-tier footwear, including Goodyear welted construction, Horween leather, and a Vibram or formal leather sole — and of course, it’s made in the USA. We suggest you roll over our hotspots to learn more on each of the parts that make this boot a masterpiece.

We sat down with Founder and Design Director, George Vlagos, for a quick chat to discuss the new Trench Boot, its genesis and some suggested wardrobe pairings. You can read our interview below.

3 Questions with George Vlagos

Founder & Design Director of Oak Street Bootmakers

Q.

Oak Street is already known for crafting heirloom-grade shoes. Any insight into what inspired you to take things further with the Trench Boots?

A.

The Trench Boot is the most exciting offering since we launched our website several years ago. With this departure from our traditional moccasin genuine handsewn construction, we wanted to offer boots that challenge the offerings of some of the best shoe makers in the world. The Trench Boot has been five years in the making — we literally went back to the drawing board and crafted countless samples time and again. We simply wanted to make the absolute best boot possible.

Q.

Talk to us briefly about the genesis of the design — we can’t help but think English, circa the first World War.

A.

Absolutely. While the Trench Boot’s name most certainly comes from the trench warfare of WWI, the design was actually inspired by my vintage boot collection. Specifically, the shape was inspired from a pair of WWI trench boots, and the silhouette from WWII field boots. The design details are truly a reflection of quality, which stems from the sturdy boots our soldiers wore in WWI and WWII.

Q.

Good footwear should pair well with many men’s wardrobe staples, but we always like to ask: any suggested menswear pairings?

A.

What makes the Trench Boot unique is that it transcends the limitations of varied niches — rather, it appeals to a broad a varied audience. Again, it’s that “one” boot that every man should have. I can’t help but to pair mine with selvedge denim from Imogene+Willie and Levi’s Vintage Clothing and shirting from Gitman Vintage and Engineered Garments.

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